Triethylamine → HCID 58010639, compound

HRID 2079241Notes

Reaction equation

HRID 2079241 reaction equation
CCN=C=NCCCN(C)C.[CH3:12][O:13][C:14]([CH2:16][C@@H:17]([OH:21])[C:18]([OH:20])=O)=[O:15].C1C=CC2N(O)N=NC=2C=1.[N:32]1([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:41]([O:40][C:38]([N:32]1[CH2:37][CH2:36][N:35]([C:18](=[O:20])[C@H:17]([OH:21])[CH2:16][C:14]([O:13][CH3:12])=[O:15])[CH2:34][CH2:33]1)=[O:39])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 643495Benzyl piperazine-1-carboxylateHCID 10654361HCID 10654361, compound

Product 1

HCID 58010639HCID 58010639, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDCI (3.6 g, 19 mmol) was added to a solution of (R)-3-(methoxycarbonyl)-2-hydroxypropanoic acid (2.8 g, 19 mmol) and HOBt (2.6 g, 19 mmol) in DMF (200 mL). After stirring this mixture for 5 min, benzyl piperazine-1-carboxylate (4.2 g, 3.6 mL, 19 mmol) and triethylamine (2.6 mL, 19 mmol) were added and stirred for 3 days at room temperature. The reaction mixture was poured into water and extracted with EtOAc. After washing the organic layers with brine and water, drying over Na2SO4 and concentrating, purification via silica gel chromatography using 0-10% MeOH/CH2Cl2 gave 4-((R)-2-hydroxy-3-methoxycarbonyl-propionyl)-piperazine-1-carboxylic acid benzyl ester as an oil (2.19 g, 33%). 1H NMR (400 MHz, CDCl3) δ 7.40-7.31 (m, 5H), 5.15 (s, 2H), 4.79-4.74 (m, 1H), 3.95 (d, J=8.0 Hz, 1H), 3.79-3.74 (m, 1H), 3.74 (s, 3H), 3.71-3.44 (m, 7H), 2.62 (d, J=5.8 Hz, 2H) ppm.

Workup

  1. stirringstirred for 3 days at room temperature
  2. extractionextracted with EtOAc
  3. washAfter washing the organic layers with brine and water
  4. dry with materialdrying over Na2SO4
  5. concentrationconcentrating
  6. custompurification via silica gel chromatography

Sources & evidence

ORD record
ord-651138203acc4e1e96eea5600e15dfec
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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